National Pineapple Upside-Down Cake Day is April 20th, and we’re flipping tradition on its head — literally. While the classic version is beloved for its caramelized pineapple rings and nostalgic charm, why not get creative this year?
With a little help from your favorite Babycakes® and Toastmaster® appliances, we’re reimagining this retro dessert in five fun and modern ways. From cake pops to waffle stacks and even air fryer renditions, there’s a pineapple upside-down treat here for everyone.
A Little History: The Origins of Pineapple Upside-Down Cake Day
No one knows exactly who started National Pineapple Upside-Down Cake Day, but the dessert itself has a history as rich as its sugary glaze.
Pineapple upside-down cake surged in popularity in the 1920s, soon after canned pineapple became widely available thanks to the Dole Pineapple Company. Creative home bakers began flipping their cakes — literally — placing pineapple rings and maraschino cherries at the bottom of the pan, then pouring batter on top. The result? A stunning, glossy cake once inverted, with buttery caramelized fruit crowning each slice.
Since then, it’s become an American classic — and April 20th gives us the perfect excuse to celebrate this nostalgic treat with a twist.
Pineapple Cake Fun Facts
-
In 1925, Dole hosted a pineapple recipe contest and received over 60,000 entries — more than 2,500 were for pineapple upside-down cake!
-
The original term “upside-down cake” was used for any cake baked with fruit on the bottom and flipped to serve — pineapple just stole the show.
-
In recent years, upside-down desserts have expanded beyond cakes: from upside-down muffins and donuts to waffles and cupcakes (yes, we’re on trend!).
1. Pineapple Upside-Down Cake Pops – Made with Babycakes® Cake Pop Maker
Mini size. Major flavor. These bite-sized pops are perfect for parties or a fun family treat.
How to Make It:
-
Mix up your favorite pineapple cake batter (or add crushed pineapple to vanilla cake mix).
-
Fill the Babycakes Cake Pop Maker with batter.
-
Once cooked, glaze the pops with a brown sugar and pineapple juice reduction.
-
Add a mini pineapple chunk on top and insert a stick — upside-down style!
Why It Works: The cake pop maker delivers perfectly round bites with a moist center — just like the best part of the traditional cake.
2. Pineapple Upside-Down Cupcakes – Made with Babycakes® Cupcake Maker
A modern twist on the full cake, these individual cupcakes keep all the signature flavors — just more fun and portable.
Recipe Highlights:
-
Layer pineapple slices and maraschino cherries with brown sugar at the bottom of each cupcake well.
-
Pour pineapple-infused batter on top and cook in the Babycakes Cupcake Maker.
-
Flip to reveal caramelized fruit perfection in under 10 minutes.
Bonus Tip: Serve warm with a scoop of coconut ice cream for tropical flair.
3. Pineapple Upside-Down Waffles – Made with Toastmaster® Flip Waffle Maker
Yes, you read that right. Waffles. This brunch bombshell takes pineapple upside-down cake to a crispy, golden new level.
Here’s How:
-
Whisk pineapple chunks and brown sugar into waffle batter.
-
Pour into your Toastmaster Flip Waffle Maker for even, golden perfection.
-
Serve flipped-side up with caramel drizzle and a cherry on top.
Perfect For: Brunch, dessert, or anytime you want something sweet and a little extra.
4. Pineapple Upside-Down Cake Bites – Toastmaster® Air Fryer Edition
Craving that classic taste with a modern twist? Say hello to the air-fried version of the iconic cake.
Steps:
-
Line ramekins or silicone muffin cups with pineapple rings and brown sugar.
-
Fill with batter and place in your Toastmaster Air Fryer.
-
Air fry at 330°F for 10–12 minutes.
-
Flip, drizzle, and serve!
Why We Love It: Faster cook time, crisped edges, and a caramelized crown without turning on the oven.
5. Sheet Pan Upside-Down Cake – Made in the Toastmaster® Toaster Oven
Want to keep it classic? Use the Toastmaster Toaster Oven for a smaller batch version of the traditional upside-down cake.
Quick How-To:
-
Layer pineapple, cherries, and brown sugar in a greased pan.
-
Pour in homemade (or boxed!) yellow cake batter.
-
Bake at 350°F in your toaster oven for 20–25 minutes.
-
Let it cool, then flip and reveal the golden, glossy top.
Pro Tip: Add rum extract to the batter for a tropical kick.
Celebrate Sweetly (and Creatively)
Whether you're team classic or team remix, National Pineapple Upside-Down Cake Day is the perfect excuse to fire up your favorite small appliance and bake something joyful. These fresh takes on a vintage favorite are easy, fun, and made even better with your Select Brands kitchen MVPs.
Ready to bake it happen?
Tag us in your creations @SelectBrands on Instagram and use #PineappleUpsideDownRemix for a chance to be featured!
